Triethylamine → HCID 19382362, compound

HRID 2400048Notes

Reaction equation

HRID 2400048 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7](=[O:12])[C:8]([CH3:11])([CH3:10])[CH3:9].C(N(CC)CC)C.[Br:20][CH2:21][C:22](Br)=[O:23]>C(Cl)Cl.C(OCC)(=O)C.[Na+].[Cl-]>[Br:20][CH2:21][C:22]([NH:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7](=[O:12])[C:8]([CH3:9])([CH3:11])[CH3:10])=[O:23]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 19382360HCID 19382360, compound

Product 1

HCID 19382362HCID 19382362, compoundYield 94.6%

Reagents, catalysts & solvents 3

HCID 5234Sodium ChlorideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

The 3-amino-2-pivaloylfuran (1.33 g, 8.0 mmol) was dissolved in methylene chloride (15 ml) under nitrogen and the solution was cooled to 0° C. Triethylamine (1.34 ml, 9.6 mmol) was added followed by 2-bromoacetyl bromide (1.94 g, 9.6 mmol) added dropwise over 1/4 hour. The mixture was stirred at ambient temperature over night. The reaction was diluted with ethyl acetate (25 ml) and saturated NaCl (10 ml). The organic layer was separated, washed with saturated NaCl, dried over Na2SO4, filtered and concentrated in vacuo. A brown oil (2.18 g) was obtained in theoretical yield.

Workup

  1. additionadded dropwise over 1/4 hour
  2. customThe organic layer was separated
  3. washwashed with saturated NaCl
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-71e470e3f63e47e29c76091e2e0ea81f
Source dataset
uspto-grants-1995_09
Patent number
US05453424

Reaction notes

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